Alkynes

• Are organic molecules made of the functional

group carbon-carbon triple bond.
• They are unsaturated hydrocarbons.
• All alkynes have the suffix –yne in the ending
of the molecule name.
• Are hydrocarbons that have the empirical
formula of CnH2n−2.
 Nomenclature
• Common system:
– Acetylene is the common name for the first
member of this group.
HC CH

• Derived system:
– Higher alkynes are named as derivatives of
acetylene
•
 Nomenclature
• IUPAC system:
– Identifying and numbering the longest chain that
contains a triple bond.
– The carbon backbone is numbered from the end that
yields the lowest positioning for the triple bond.
– Changing the suffix:
• The position of the triple bond is indicated using the
position of the carbon in the bond with the lower
backbone number.
• The suffix for the compound is changed to “-yne”.
 Preparation of alkynes
1. Dehydrohalogenation of vicinal dihalides:
– Treatment of vicinal dihalides with alcoholic KOH followed by
NaNH2
– The loss of a hydrogen atom and a halogen atom from
adjacent alkane carbon atoms leads to the formation of an
alkene.
– The loss of additional hydrogen and halogen atoms from the
double‐bonded carbon atoms leads to alkyne formation.
– The halogen atoms may be located on the same carbon (a
geminal dihalide) or on adjacent carbons (a vicinal dihalide).
 Preparation of alkynes
2. Dehalogenation of tetrahalides:
– By heating with zinc dust in alcohol

3. Reaction of Calcium carbide with water.

 Important reactions of alkynes
1. Addition reactions
a. Hydrogenation
b. Halogenation
c. Addition of halogen acids
d. Addition of hydrogen cyanide
e. Addition of hypohalous acids
f. Hydration
g. Polymerization
h. Combustion
i. Reaction with KMnO4
2. Salt formation
a. Acetylides formation
b. Formation of Cu2+ and Ag+ acetylides
 Hydration of alkynes
• Unlike the additions to double bonds which give alcohol
products, addition of water to alkynes gives ketone products
( except for acetylene which yields acetaldehyde ).
• The initial product from the addition of water to an alkyne is
an enol (a compound having a hydroxyl substituent attached
to a double-bond), and this immediately rearranges (ex.
Rearrangement reaction) to the more stable keto tautomer.
 Polymerization of alkynes
• Conjugated linear polyacetylenes are important materials
for:
– electrical conductivity,
– paramagnetic susceptibility,
– optical nonlinearity,
– photoconductivity,
– gas permeability,
– liquid crystallinity
• Access to a wide variety of new cyclic polymers is now
possible by simply choosing the appropriate alkyne
monomer.
 Salt formation
a. Alkynes salts are called “Acetylides” .
a. They can be formed by replacing H atom in alkynes with the metal
atom.
b. Sod. acetylide reacts with primary alkyl halides to form higher
alkynes.
b. Formation of Cu2+ and Ag+ acetylides:
c. Copper acetylide can be prepared by treating acetylene with
ammoniacal solutions of cuprous chloride and silver nitrate.
d. This reaction produces reddish and white solid precipitates
respectively.
e. Dry copper acetylide is a heat and shock sensitive high explosive,
more thermally sensitive than silver acetylide.
f. Dry acetylides can be decomposed by HNO3 to regenerate alkynes.